benzatropine Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
atropine derivatives 333 86-13-5

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • cogentin
  • benztropine mesilate
  • benzatropine
  • benztropine
  • tropine benzohydryl ether
  • benztropine mesylate
A centrally active muscarinic antagonist that has been used in the symptomatic treatment of PARKINSON DISEASE. Benztropine also inhibits the uptake of dopamine.
  • Molecular weight: 307.44
  • Formula: C21H25NO
  • CLOGP: 3.52
  • LIPINSKI: 0
  • HAC: 2
  • HDO: 0
  • TPSA: 12.47
  • ALOGS: -5.41
  • ROTB: 4

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
2 mg O
2 mg P

ADMET properties:

PropertyValueReference
MRTD (Maximum Recommended Therapeutic Daily Dose) 0.21 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Hosey CM, Chan R, Benet LZ
BA (Bioavailability) 29 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

DateAgencyCompanyOrphan
March 5, 1954 FDA

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Granulocytopenia 344.12 18.05 96 9452 5464 53334054
Completed suicide 291.97 18.05 222 9326 137979 53201539
Tardive dyskinesia 180.29 18.05 64 9484 8006 53331512
Schizophrenia 175.94 18.05 67 9481 10212 53329306
Psychotic disorder 160.27 18.05 81 9467 24304 53315214
Toxicity to various agents 128.15 18.05 176 9372 219422 53120096
Neuroleptic malignant syndrome 125.51 18.05 55 9493 11978 53327540
Extrapyramidal disorder 114.35 18.05 52 9496 12350 53327168
Paranoia 108.82 18.05 49 9499 11375 53328143
Hallucination, auditory 107.40 18.05 49 9499 11724 53327794
Sedation 72.06 18.05 52 9496 29623 53309895
Dystonia 67.69 18.05 37 9511 12984 53326534
Oculogyric crisis 66.66 18.05 20 9528 1468 53338050
Agitation 66.03 18.05 66 9482 58560 53280958
Muscle rigidity 65.36 18.05 34 9514 10807 53328711
Blood prolactin increased 58.60 18.05 22 9526 3217 53336301
Tremor 54.73 18.05 88 9460 125648 53213870
Catatonia 53.88 18.05 22 9526 4018 53335500
Schizoaffective disorder 51.40 18.05 18 9530 2159 53337359
Ileus paralytic 51.08 18.05 22 9526 4589 53334929
Suicidal ideation 50.28 18.05 58 9490 60453 53279065
Dyskinesia 49.68 18.05 43 9505 31790 53307728
Clonus 49.27 18.05 21 9527 4270 53335248
Aggression 47.85 18.05 37 9511 23366 53316152
Akathisia 46.34 18.05 25 9523 8546 53330972
Delusion 46.06 18.05 28 9520 11981 53327537
Leukopenia 45.88 18.05 61 9487 73402 53266116
Hyperreflexia 44.35 18.05 21 9527 5459 53334059
Myocarditis 43.84 18.05 24 9524 8444 53331074
Drooling 43.05 18.05 18 9530 3490 53336028
Galactorrhoea 40.80 18.05 18 9530 3977 53335541
Cardiac arrest 37.28 18.05 63 9485 93604 53245914
Abnormal behaviour 37.11 18.05 31 9517 21835 53317683
Salivary hypersecretion 36.83 18.05 20 9528 6923 53332595
Treatment noncompliance 36.82 18.05 37 9511 32998 53306520
Amaurosis 36.35 18.05 10 9538 538 53338980
Hyperthermia 35.51 18.05 21 9527 8548 53330970
Confusional state 34.46 18.05 94 9454 194127 53145391
Haemoglobin urine 33.53 18.05 7 9541 113 53339405
Drug interaction 32.96 18.05 100 9448 219229 53120289
Hallucination 32.52 18.05 44 9504 53794 53285724
Encephalitis autoimmune 31.69 18.05 11 9537 1285 53338233
Joint swelling 31.16 18.05 3 9545 234635 53104883
Mydriasis 30.14 18.05 21 9527 11305 53328213
Amenorrhoea 28.85 18.05 19 9529 9330 53330188
Arthralgia 28.84 18.05 22 9526 439761 52899757
Torsade de pointes 27.54 18.05 21 9527 12984 53326534
Psychiatric decompensation 27.39 18.05 10 9538 1352 53338166
Dysarthria 27.35 18.05 35 9513 40533 53298985
Parkinsonism 27.05 18.05 18 9530 8995 53330523
Cardio-respiratory arrest 26.73 18.05 42 9506 58716 53280802
Electrocardiogram QT prolonged 26.61 18.05 41 9507 56362 53283156
Toxic encephalopathy 25.81 18.05 15 9533 5912 53333606
Diabetes mellitus 25.17 18.05 39 9509 53860 53285658
Mental disorder 24.80 18.05 26 9522 24350 53315168
Hyperprolactinaemia 24.68 18.05 12 9536 3303 53336215
Cognitive disorder 24.65 18.05 35 9513 44743 53294775
Suspected suicide 24.34 18.05 13 9535 4355 53335163
Lipids decreased 24.29 18.05 4 9544 15 53339503
Facial paralysis 24.07 18.05 20 9528 13973 53325545
Red blood cells urine 23.95 18.05 7 9541 469 53339049
Diarrhoea 22.68 18.05 49 9499 625497 52714021
Eosinophil count abnormal 22.55 18.05 7 9541 576 53338942
Mental status changes 21.88 18.05 31 9517 39540 53299978
Restlessness 21.78 18.05 26 9522 28061 53311457
Schizoaffective disorder bipolar type 21.47 18.05 5 9543 136 53339382
Hypersensitivity 20.73 18.05 6 9542 210659 53128859
Pain 20.57 18.05 47 9501 588351 52751167
Mania 20.54 18.05 17 9531 11812 53327706
Abdominal discomfort 20.50 18.05 7 9541 221055 53118463
Flat affect 19.93 18.05 8 9540 1397 53338121
Bipolar disorder 19.87 18.05 14 9534 7672 53331846
Areflexia 19.67 18.05 10 9538 3026 53336492
Pneumonia aspiration 19.15 18.05 27 9521 34274 53305244
Screaming 18.95 18.05 10 9538 3267 53336251

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Granulocytopenia 529.11 18.88 161 11125 6354 32495886
Completed suicide 219.76 18.88 211 11075 92306 32409934
Tardive dyskinesia 183.86 18.88 70 11216 5461 32496779
Neuroleptic malignant syndrome 172.68 18.88 95 11191 17400 32484840
Extrapyramidal disorder 158.54 18.88 79 11207 11816 32490424
Myocarditis 154.55 18.88 77 11209 11513 32490727
Psychotic disorder 146.03 18.88 94 11192 22926 32479314
Toxicity to various agents 130.04 18.88 226 11060 177815 32324425
Schizophrenia 123.34 18.88 63 11223 9921 32492319
Agitation 98.48 18.88 110 11176 57126 32445114
Hallucination, auditory 96.05 18.88 54 11232 10296 32491944
Dystonia 94.74 18.88 54 11232 10569 32491671
Akathisia 85.80 18.88 44 11242 6981 32495259
Tremor 77.99 18.88 117 11169 81160 32421080
Sedation 71.74 18.88 56 11230 18470 32483770
Cogwheel rigidity 70.96 18.88 24 11262 1326 32500914
Drooling 69.17 18.88 30 11256 3267 32498973
Galactorrhoea 65.18 18.88 17 11269 376 32501864
Dystonic tremor 65.06 18.88 15 11271 194 32502046
Device leakage 62.35 18.88 31 11255 4605 32497635
Abnormal behaviour 60.02 18.88 59 11227 26407 32475833
Hyperprolactinaemia 59.83 18.88 21 11265 1297 32500943
Leukopenia 58.27 18.88 87 11199 60035 32442205
Muscle rigidity 54.91 18.88 39 11247 11147 32491093
Paranoia 53.82 18.88 38 11248 10761 32491479
Treatment noncompliance 53.23 18.88 56 11230 27146 32475094
Drug abuse 52.10 18.88 97 11189 80146 32422094
Aggression 51.70 18.88 66 11220 39323 32462917
Syringe issue 50.46 18.88 25 11261 3686 32498554
Parkinsonism 49.52 18.88 32 11254 7837 32494403
Schizoaffective disorder 48.71 18.88 18 11268 1290 32500950
Anticholinergic syndrome 47.30 18.88 16 11270 884 32501356
Restlessness 44.76 18.88 49 11237 24832 32477408
Drug interaction 44.41 18.88 171 11115 218014 32284226
Product dose omission issue 44.37 18.88 105 11181 102470 32399770
Inappropriate schedule of product administration 43.93 18.88 66 11220 45759 32456481
Priapism 43.49 18.88 25 11261 4966 32497274
Antipsychotic drug level increased 42.68 18.88 22 11264 3524 32498716
Catatonia 42.14 18.88 24 11262 4684 32497556
Blood prolactin increased 38.29 18.88 16 11270 1589 32500651
Delusion 36.97 18.88 33 11253 13075 32489165
Dyskinesia 36.54 18.88 43 11243 23560 32478680
Mental status changes 36.43 18.88 55 11231 38282 32463958
Suicidal ideation 35.29 18.88 54 11232 38029 32464211
Drug level increased 35.17 18.88 39 11247 20041 32482199
Agranulocytosis 35.07 18.88 42 11244 23435 32478805
Eosinophilic pleural effusion 32.48 18.88 9 11277 252 32501988
Blood creatine phosphokinase increased 32.05 18.88 57 11229 45419 32456821
Sinus tachycardia 30.69 18.88 33 11253 16381 32485859
Delirium 29.50 18.88 54 11232 43992 32458248
Lethargy 29.47 18.88 52 11234 41176 32461064
Homicidal ideation 27.64 18.88 15 11271 2665 32499575
Head titubation 27.47 18.88 8 11278 269 32501971
Musculoskeletal stiffness 27.39 18.88 49 11237 39215 32463025
Diarrhoea 26.84 18.88 54 11232 364748 32137492
Blood pH decreased 26.72 18.88 14 11272 2319 32499921
Mania 26.67 18.88 24 11262 9608 32492632
Blood triglycerides increased 26.65 18.88 29 11257 14590 32487650
Oculogyric crisis 26.51 18.88 12 11274 1445 32500795
Overdose 26.27 18.88 78 11208 86999 32415241
Febrile neutropenia 25.98 18.88 5 11281 119561 32382679
Needle issue 25.47 18.88 17 11269 4392 32497848
Bipolar disorder 24.86 18.88 16 11270 3890 32498350
Antipsychotic drug level decreased 24.68 18.88 10 11276 918 32501322
Parasomnia 24.57 18.88 8 11278 392 32501848
Type 2 diabetes mellitus 24.07 18.88 28 11258 15144 32487096
Device malfunction 24 18.88 22 11264 9017 32493223
Weight increased 23.42 18.88 73 11213 83590 32418650
Haemophagocytic lymphohistiocytosis 21.56 18.88 23 11263 11312 32490928
Gynaecomastia 20.61 18.88 20 11266 8799 32493441
Globulins decreased 20.51 18.88 6 11280 205 32502035
Troponin increased 20.39 18.88 21 11265 9921 32492319
Salivary hypersecretion 20.15 18.88 19 11267 8069 32494171
Somnolence 19.93 18.88 80 11206 103717 32398523
Faecaloma 19.76 18.88 15 11271 4741 32497499

Pharmacologic Action:

SourceCodeDescription
ATC N04AC01 NERVOUS SYSTEM
ANTI-PARKINSON DRUGS
ANTICHOLINERGIC AGENTS
Ethers of tropine or tropine derivatives
FDA MoA N0000000207 Histamine Receptor Antagonists
FDA MoA N0000175370 Cholinergic Antagonists
FDA EPC N0000175574 Anticholinergic
CHEBI has role CHEBI:48407 antiparkinson agent
CHEBI has role CHEBI:48876 Antimuskarinika
CHEBI has role CHEBI:50370 parasympatholytics
CHEBI has role CHEBI:66956 antidyskinetic drugs
CHEBI has role CHEBI:146270 oneirogens
CHEBI has role CHEBI:149553 anti-coronaviral agents
MeSH PA D018726 Anti-Dyskinesia Agents
MeSH PA D000978 Antiparkinson Agents
MeSH PA D002491 Central Nervous System Agents
MeSH PA D018678 Cholinergic Agents
MeSH PA D018680 Cholinergic Antagonists
MeSH PA D015259 Dopamine Agents
MeSH PA D018765 Dopamine Uptake Inhibitors
MeSH PA D049990 Membrane Transport Modulators
MeSH PA D018727 Muscarinic Antagonists
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D014179 Neurotransmitter Uptake Inhibitors
MeSH PA D010276 Parasympatholytics
MeSH PA D018373 Peripheral Nervous System Agents
FDA EPC N0000175750 Antihistamine

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Postencephalitic parkinsonism indication 19972008 DOID:14332
Parkinsonism indication 32798002
Parkinson's disease indication 49049000 DOID:14330
Extrapyramidal disease indication 76349003
Arteriosclerotic Parkinsonism indication
Urinary tract obstruction contraindication 7163005 DOID:5200
Chronic obstructive lung disease contraindication 13645005 DOID:3083
Severe chronic ulcerative colitis contraindication 14311001
Disorder of autonomic nervous system contraindication 15241006
Toxic megacolon contraindication 28536002 DOID:1770
Atony of colon contraindication 29479008
Shigellosis contraindication 36188001
Hypertensive disorder contraindication 38341003 DOID:10763
Conduction disorder of the heart contraindication 44808001
Low blood pressure contraindication 45007003
Achalasia of esophagus contraindication 45564002 DOID:9164
Chronic heart failure contraindication 48447003
Dysuria contraindication 49650001
Paralytic ileus contraindication 55525008 DOID:8442
Ulcerative colitis contraindication 64766004 DOID:8577
Hiatal hernia contraindication 84089009 DOID:12642
Open-angle glaucoma contraindication 84494001 DOID:1067
Kidney disease contraindication 90708001 DOID:557
Thyrotoxicosis contraindication 90739004 DOID:7997
Myasthenia gravis contraindication 91637004 DOID:437
Tardive dyskinesia contraindication 102449007
Dysentery contraindication 111939009
Gastrointestinal obstruction contraindication 126765001
Bleeding contraindication 131148009
Gastroesophageal reflux disease contraindication 235595009 DOID:8534
Disease of liver contraindication 235856003 DOID:409
Benign prostatic hyperplasia contraindication 266569009
Retention of urine contraindication 267064002
Fever contraindication 386661006
Angle-closure glaucoma contraindication 392291006 DOID:13550
Pseudomembranous enterocolitis contraindication 397683000
Gastric ulcer contraindication 397825006 DOID:10808
Disorder of coronary artery contraindication 414024009

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 9.86 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Muscarinic acetylcholine receptor M1 GPCR ANTAGONIST Ki 9.64 WOMBAT-PK CHEMBL
Sigma non-opioid intracellular receptor 1 Membrane receptor Ki 7.23 DRUG MATRIX
Sodium-dependent serotonin transporter Transporter IC50 4.62 CHEMBL
Sodium-dependent noradrenaline transporter Transporter Ki 5.86 DRUG MATRIX
5-hydroxytryptamine receptor 2A GPCR Ki 8.16 DRUG MATRIX
5-hydroxytryptamine receptor 2B GPCR Ki 6.90 DRUG MATRIX
5-hydroxytryptamine receptor 2C GPCR Ki 7.50 DRUG MATRIX
5-hydroxytryptamine receptor 6 GPCR Ki 5.89 DRUG MATRIX
Alpha-2B adrenergic receptor GPCR Ki 7.52 DRUG MATRIX
D(3) dopamine receptor GPCR Ki 6.65 DRUG MATRIX
Histamine H1 receptor GPCR Ki 8.96 WOMBAT-PK
Histamine H2 receptor GPCR Ki 5.93 DRUG MATRIX
Muscarinic acetylcholine receptor M2 GPCR ANTAGONIST Ki 8.85 WOMBAT-PK
Muscarinic acetylcholine receptor M3 GPCR ANTAGONIST Ki 8.96 WOMBAT-PK
Muscarinic acetylcholine receptor M4 GPCR ANTAGONIST Ki 8.96 WOMBAT-PK
Muscarinic acetylcholine receptor M5 GPCR ANTAGONIST Ki 8.55 WOMBAT-PK
Alpha-2C adrenergic receptor GPCR Ki 7.24 DRUG MATRIX
Sodium-dependent dopamine transporter Transporter Kd 7.25 WOMBAT-PK
Alpha-1D adrenergic receptor GPCR Ki 7.59 DRUG MATRIX
Alpha-2A adrenergic receptor GPCR Ki 6.69 DRUG MATRIX
Sodium-dependent neutral amino acid transporter B(0)AT1 Transporter INHIBITOR IC50 4.36 IUPHAR
Alpha-1B adrenergic receptor GPCR Ki 7.39 DRUG MATRIX
Membrane-associated progesterone receptor component 1 Membrane receptor Ki 6.95 DRUG MATRIX
Alpha-1A adrenergic receptor GPCR IC50 6.85 CHEMBL
Muscarinic acetylcholine receptor M2 GPCR Ki 8.59 CHEMBL
Muscarinic acetylcholine receptor M1 GPCR Ki 9.23 CHEMBL
Sodium-dependent serotonin transporter Transporter Ki 5.29 CHEMBL
Sodium-dependent dopamine transporter Transporter Ki 6.93 CHEMBL

External reference:

IDSource
D00778 KEGG_DRUG
132-17-2 SECONDARY_CAS_RN
1424 RXNORM
C0005098 UMLSCUI
CHEBI:3048 CHEBI
CXQ PDB_CHEM_ID
CHEMBL1201203 ChEMBL_ID
CHEMBL1200383 ChEMBL_ID
DB00245 DRUGBANK_ID
7601 IUPHAR_LIGAND_ID
292 INN_ID
1NHL2J4X8K UNII
1201549 PUBCHEM_CID
3130 MMSL
4264 MMSL
563 MMSL
d00175 MMSL
001647 NDDF
004667 NDDF
29527005 SNOMEDCT_US
372846002 SNOMEDCT_US
77390008 SNOMEDCT_US
D001590 MESH_DESCRIPTOR_UI
4017824 VANDF
4019630 VANDF

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 0143-9233 INJECTION 1 mg INTRAMUSCULAR ANDA 15 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 0143-9729 INJECTION 1 mg INTRAMUSCULAR ANDA 14 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 0603-2437 TABLET 0.50 mg ORAL ANDA 16 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 0603-2438 TABLET 1 mg ORAL ANDA 16 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 0603-2439 TABLET 2 mg ORAL ANDA 16 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 0615-8210 TABLET 0.50 mg ORAL ANDA 16 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 0615-8211 TABLET 1 mg ORAL ANDA 16 sections
benztropine mesylate HUMAN PRESCRIPTION DRUG LABEL 1 0615-8352 TABLET 2 mg ORAL ANDA 16 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 0832-1080 TABLET 0.50 mg ORAL ANDA 15 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 0832-1081 TABLET 1 mg ORAL ANDA 15 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 0832-1082 TABLET 2 mg ORAL ANDA 15 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 0904-6788 TABLET 0.50 mg ORAL ANDA 16 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 0904-6789 TABLET 2 mg ORAL ANDA 16 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 0904-6790 TABLET 1 mg ORAL ANDA 16 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 10135-606 TABLET 0.50 mg ORAL ANDA 15 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 10135-607 TABLET 1 mg ORAL ANDA 15 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 10135-608 TABLET 2 mg ORAL ANDA 15 sections
benztropine mesylate HUMAN PRESCRIPTION DRUG LABEL 1 10858-011 INJECTION 1 mg INTRAMUSCULAR ANDA 1 sections
Benztropine Mesylate Injection, USP HUMAN PRESCRIPTION DRUG LABEL 1 14789-300 INJECTION 1 mg PARENTERAL ANDA 11 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 17478-012 INJECTION 1 mg INTRAVENOUS NDA authorized generic 16 sections
BENZTROPINE MESYLATE HUMAN PRESCRIPTION DRUG LABEL 1 21695-286 TABLET 2 mg ORAL ANDA 15 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 31722-218 TABLET 0.50 mg ORAL ANDA 16 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 31722-219 TABLET 1 mg ORAL ANDA 16 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 31722-220 TABLET 2 mg ORAL ANDA 16 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 43353-580 TABLET 1 mg ORAL ANDA 16 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 43353-707 TABLET 0.50 mg ORAL ANDA 16 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 43353-796 TABLET 1 mg ORAL ANDA 16 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 43353-913 TABLET 0.50 mg ORAL ANDA 16 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 50090-3116 TABLET 1 mg ORAL ANDA 15 sections
BENZTROPINE MESYLATE HUMAN PRESCRIPTION DRUG LABEL 1 50090-3882 TABLET 2 mg ORAL ANDA 13 sections